Org. Lett., 7 (22), 4815 -4818, 2005. 10.1021/ol051496y S1523-7060(05)01496-3
Web Release Date: September 27, 2005

Copyright © 2005 American Chemical Society

Dendrimeric Molecular Transporters: Synthesis and Evaluation of Tunable Polyguanidino Dendrimers That Facilitate Cellular Uptake

Paul A. Wender,* Erik Kreider, Erin T. Pelkey, Jonathan Rothbard,* and Christopher L. VanDeusen*

Department of Chemistry and Department of Molecular Pharmacology, Stanford University, Stanford, California 94305-5080, and Cellgate, Inc., 552 Del Rey Avenue, Sunnyvale, California 94086

wenderp@stanford.edu

Received June 27, 2005

Revised September 14, 2005

Abstract:

Nine fluorescently labeled structurally varied polyguanidino dendrimers based on diamino acid monomeric units were individually synthesized in an efficient, scalable sequence using a trifluoroacetamide protecting group-perguanidinylation strategy. While the dendrimers varied significantly in their ability to enter a human lymphocyte cell line, the best transporters out-performed an oligoarginine reference standard.


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